CN103193672B - Distillation method of oxime - Google Patents
Distillation method of oxime Download PDFInfo
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- CN103193672B CN103193672B CN201310077469.0A CN201310077469A CN103193672B CN 103193672 B CN103193672 B CN 103193672B CN 201310077469 A CN201310077469 A CN 201310077469A CN 103193672 B CN103193672 B CN 103193672B
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Abstract
The present invention relates to a distillation method of oxime. Tower bottom materials are usually heated by still distillation, a U-shaped outer tube or a rotary film evaporator, long-term operation of the tower bottom is easy to coking, and the distillation efficiency is low. The invention is characterized in that: in the distillation and separation section of oxime, at least one high boiling point solvent is added in the distillation process, the content of the high boiling point solvent in the tower bottom is maintained in proportional to that of oxime, and finally oxime is effectively separated by distillation. Oxime is fed into a rectifying tower, and is distilled at an absolute pressure of 0-0.4 MPa and at 20-300 DEG C to collect fractions. The unevaporated liquid left in the tower bottom is subjected to the processes of removing water and impurities, and is recycled to the rectifying tower as a high boiling point solvent. The present invention can reduce total production costs, simplify operation processes, prevent the product from coking in the tower bottom or decomposing due to overheating, ensure product distillation to be efficient, continuous, safe and stable, and improve product quality.
Description
Technical field
The present invention relates to organic chemistry purification technique field, particularly a kind of distillating method of oxime.
Background technology
Oxime is the widely used fine chemical product of a class.For example Diacetylmonoxime is used in coating as anti skinning agent, and acetoxime is used in thermal boiler water deoxygenation as oxygen scavenger, and ethylidenehydroxylamine is as the intermediate of production MHTA agricultural chemicals, and cyclohexanone-oxime is the intermediate of producing nylon-6 monomer ε-caprolactam.
The industrial separating-purifying that relates to oxime is mainly undertaken by rectifying tower.But be the rectifying problem that oxime recovery process in the synthetic or oxime compounds application process of oxime all exists oxime.The rectifying problem of oxime is due to the very easily coking blocking pipe of oxime and equipment, causes rectifier unit to be difficult to normal operation, needs periodically cleaning, and maintenance service is loaded down with trivial details.And batch distillation and continuous rectification are all difficult to avoid oxime coking in tower reactor.
The rectifying tower of existing routine heats tower reactor material with still distillation, the heating of U-shaped outer tube or rotary film evaporator conventionally, but has respectively following shortcoming:
1. kettle-type reboiler can not maximize because of production equipment that heat-transfer surface is limit, and very easily coking is coking, common 3 ~ 7 days must cleaning once.
2.U shape pipe outer tube heating heat-transfer effect is better, but cannot avoid material coking on the heating coil of stratiform coiling and tower reactor wall, needs an outer tube of cleaning in 3 ~ 30 days.
3., though rotary film evaporator is better than the above two, also need 7 ~ 30 days cleaning single vaporization devices.
Therefore, to also not having a kind ofly can make that tower reactor long-term operation is not coking, distillation efficiency is high, the distillating method of constant product quality for the rectifying of oxime and oxime compounds so far.
Summary of the invention
The present invention is directed to above-mentioned defect, a kind of distillating method of oxime is provided, can reduce production costs, the technique that simplifies the operation, prevents that product is coking or decompose because of overheated in tower reactor, guarantees that the fractionation by distillation of product becomes efficiently, continuously, safety, stable, Improving The Quality of Products.
For this reason, the present invention takes following technical scheme, a kind of distillating method of oxime, it is characterized in that the fractionation by distillation workshop section at oxime, at least add a kind of high boiling solvent in still-process, the content and the oxime that maintain high boiling solvent in tower reactor are proportional, distill, finally effectively isolate oxime.Specifically realize by the following technical solutions:
The first step: by massfraction than the oxime in solution: high boiling solvent is 1%:(0.02% ~ 99%), be ready to appropriate high boiling solvent, then, high boiling solvent can add in oxime, fully mix with oxime, also can be directly join rectifying tower from any a section of tower.Described oxime is the oximes such as acetoxime, Diacetylmonoxime, cyclohexanone-oxime, benzaldoxime, methyl isobutyl ketoxime, methyl isoamyl ketoxime, 2 pentanone oxime, diphenylketoxime, methyl-prop ketoxime, citronellal oxime, p-Hydroxyacetophenone oxime, its general formula is R1 (C=NOH) R2, wherein R1 and R2 represent that carbonatoms is 1 ~ 10 alkyl, and described high boiling solvent is the organic solvent that is greater than the mixture of one or several solvents such as 5 DEG C of above petroleum hydrocarbons of oxime boiling point, high boiling point alcohols, ethers, ester class.Be preferably greater than the organic solvent of the mixture of one or several solvents such as 15 ~ 120 DEG C of petroleum hydrocarbons of oxime boiling point, high boiling point alcohols, ethers, ester class.
Second step: oxime is added to rectifying tower, distill at absolute pressure is 0 ~ 0.4MPa and 20 ~ 300 DEG C, collect cut.Gained cut is refining oxime.This operation can be that the oxime solution that contains high boiling solvent is added to rectifying tower, can be also the rectifying tower that adds tower reactor to contain high boiling solvent oxime,
The 3rd step: not steaming the liquid of staying tower reactor in second step, through dewatering, removal of impurities processing, is back to rectifying tower as high boiling solvent and recycles.
The present invention is containing acetoxime, Diacetylmonoxime, cyclohexanone-oxime, benzaldoxime, methyl isobutyl ketoxime, methyl isoamyl ketoxime, 2 pentanone oxime, diphenylketoxime, methyl-prop ketoxime, citronellal oxime, p-Hydroxyacetophenone oxime etc. wherein in a kind of solution of oxime, add high boiling solvent, or directly add high boiling solvent in tower reactor, distill, finally effectively isolate oxime.Solve conventional oxime and in rectifying tower, carried out in distillation procedure easily coking, the easy problem of crossing thermolysis.
Compared with prior art, the technology of the present invention has following remarkable advantage:
1. thoroughly avoided oxime coking obstruction to water back causing in still kettle, effectively prevented that solution local superheating from making oxime decomposes wherein.Batch fractionating and continuous rectification are all suitable for, and still-process is realized continuously, long period operation, has improved production efficiency.
Easy and simple to handle, the safety and environmental protection of this method, avoided the infringement to equipment, improved separation efficiency and quality product, be a kind of novel distillating method effectively.
3. after pair distillation, high boiling solvent carries out recycling use, and regularly removal of impurities, has reduced production cost, greatly reduces vinasse quantity discharged.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.
Embodiment 1
By massfraction than the oxime in solution: high boiling solvent is 1%:0.02%, take purity and be 1.46 grams of 99.6% glycerine, join in the solution that 109 grams of acetoxime content are 66.9%, stir after 10 minutes through agitator, distill, control tower bottom of rectifying tower temperature at 50 ~ 60 DEG C, absolute pressure is 0.01MPa, reflux ratio is 3, and after approximately 30 minutes, distillation finishes.Collect 70 grams of cuts, oxime content is 99.8%, and in cut, foreign matter content is low.
Embodiment 2
By massfraction than the oxime in solution: high boiling solvent is 1%:5%, take purity and be 364.6 grams of 99.6% glycerine, join in the solution that 109 grams of acetoxime content are 66.9%, stir after 8 minutes through agitator, distill, control tower bottom of rectifying tower temperature at 110 ~ 120 DEG C, absolute pressure is that 0.05MPa reflux ratio is 2.5, and after approximately 50 minutes, distillation finishes.Collect 71.3 grams of cuts, oxime content is 99.9%, and in cut, foreign matter content is low.
Embodiment 3
By massfraction than the oxime in solution: high boiling solvent is 1%:10%, take purity and be 729.2 grams of 99.6% glycerine, join in the solution that 109 grams of acetoxime content are 66.9%, stir after 5 minutes through agitator, distill, control tower bottom of rectifying tower temperature at 150 ~ 160 DEG C, absolute pressure is that 0.09MPa reflux ratio is 2, and after approximately 60 minutes, distillation finishes.Collect 72.5 grams of cuts, oxime content is 99.86%, and in cut, foreign matter content is low.
Embodiment 4
By massfraction than the oxime in solution: high boiling solvent is 1%:0.1%, take purity and be 8.70 grams of 99.9% ethylene glycol, join in the solution that 123 grams of Diacetylmonoxime content are 70.7%, stir after 10 minutes through agitator, distill, control tower bottom of rectifying tower temperature at 80 ~ 90 DEG C, absolute pressure is 0.01MPa, reflux ratio is 3.5, and after approximately 30 minutes, distillation finishes.Collect 86.2 grams of cuts, oxime content is 99.91%, and in cut, foreign matter content is low.
Embodiment 5
By massfraction than the oxime in solution: high boiling solvent is 1%:60%, take purity and be 521.8 grams of 99.9% ethylene glycol, join in the solution that 12.3 grams of Diacetylmonoxime content are 70.7%, stir after 8 minutes through agitator, distill, control tower bottom of rectifying tower temperature at 120 ~ 130 DEG C, absolute pressure is 0.05MPa, reflux ratio is 3, and after approximately 50 minutes, distillation finishes.Collect 86.1 grams of cuts, oxime content is 99.93%, and in cut, foreign matter content is low.
Embodiment 6
By massfraction than the oxime in solution: high boiling solvent is 1%:90%, take purity and be 782.6 grams of 99.9% ethylene glycol, join in the solution that 12.3 grams of Diacetylmonoxime content are 70.7%, stir after 5 minutes through agitator, distill, control tower bottom of rectifying tower temperature at 160 ~ 170 DEG C, absolute pressure is 0.08MPa, reflux ratio is 2, and after approximately 60 minutes, distillation finishes.Collect 86.8 grams of cuts, oxime content is 99.86%, and in cut, foreign matter content is low.
Embodiment 7
By massfraction than the oxime in solution: high boiling solvent is 1%:0.05%, take purity and be 5.65 grams of 99.6% glycerine, join in the solution that 149 grams of cyclohexanone-oxime content are 75.8%, add again 10 grams of heavy aromatic solvent oils that contain C10, stir after 10 minutes through agitator, distill, control tower bottom of rectifying tower temperature at 100 ~ 110 DEG C, absolute pressure is 0.01MPa, and reflux ratio is 4, and after approximately 30 minutes, distillation finishes.Collect 111.5 grams of cuts, oxime content is 99.83%, and in cut, foreign matter content is low.
Embodiment 8
By massfraction than the oxime in solution: high boiling solvent is 1%:25%, take purity and be 282.3 grams of 99.6% glycerine, join in the solution that 14.9 grams of cyclohexanone-oxime content are 75.8%, add again 50 grams of heavy aromatic solvent oils that contain C10, stir after 8 minutes through agitator, distill, control tower bottom of rectifying tower temperature at 150 ~ 160 DEG C, absolute pressure is 0.04MPa, and reflux ratio is 2.5, and after approximately 60 minutes, distillation finishes.Collect 112.7 grams of cuts, oxime content is 99.91%, and in cut, foreign matter content is low.
Embodiment 9
By massfraction than the oxime in solution: high boiling solvent is 1%:60%, take purity and be 677.6 grams of 99.6% glycerine, join in the solution that 14.9 grams of cyclohexanone-oxime content are 75.8%, add again 100 grams of heavy aromatic solvent oils that contain C10, stir after 5 minutes through agitator, distill, control tower bottom of rectifying tower temperature at 180 ~ 190 DEG C, absolute pressure is 0.07MPa, and reflux ratio is 2, and after approximately 60 minutes, distillation finishes.Collect 112.5 grams of cuts, oxime content is 99.88%, and in cut, foreign matter content is low.
Embodiment 10
By massfraction than the oxime in solution: high boiling solvent is 1%:5%, take purity and be 364.6 grams of 99% ethylene glycol dibutyl ethers, join in the solution that 109 grams of acetoxime content are 66.9%, stir after 10 minutes through agitator, distill, control tower bottom of rectifying tower temperature at 110 ~ 120 DEG C, absolute pressure is 0.05MPa, reflux ratio is 1, and after approximately 50 minutes, distillation finishes.Collect 72.3 grams of cuts, oxime content is 99.90%, and in cut, foreign matter content is low.
Embodiment 11
Join mixing solutions same as Example 1 by the proportioning raw materials in example 1 and reagent dosage, add in rectifying tower and distill continuously with certain inlet amount, control tower bottom of rectifying tower temperature at 50 ~ 60 DEG C, absolute pressure is 0.01MPa, reflux ratio is 3, discharges after still liquid is processed and returns in tower and recycle simultaneously, timing acquiring cut assay with certain flow, oxime content is 99.78% ~ 99.93%, and foreign matter content is few.Column efficiency is stable, moves continuously 1 year tower reactor not coking.
Embodiment 12
Be ready to respectively reagent by the proportioning raw materials in example 2 and consumption, glycerine is joined to tower reactor, stock liquid adds in tower and distills, control tower bottom of rectifying tower temperature at 110 ~ 120 DEG C, absolute pressure is 0.05MPa, and reflux ratio is 2.5, end to be distilled, then add the stock liquid of same amount to distill.Collect respectively cut assay, oxime content is 99.85 ~ 99.96%, and in cut, foreign matter content is low.Within every 60 days, change a tower reactor solvent, column efficiency is stable, and in operational process, tower reactor is not coking.
Embodiment 13
Join mixing solutions same as Example 4 by the proportioning raw materials in example 4 and reagent dosage, add in rectifying tower and distill continuously with certain inlet amount, control tower bottom of rectifying tower temperature at 80 ~ 90 DEG C, absolute pressure is 0.01MPa, reflux ratio is 3.5, discharges after still liquid is processed and returns in tower and recycle simultaneously, timing acquiring cut assay with certain flow, oxime content is 99.86% ~ 99.97%, and foreign matter content is few.Column efficiency is stable, moves continuously 1 year tower reactor not coking.
Embodiment 14
Be ready to respectively reagent by the proportioning raw materials in example 5 and consumption, ethylene glycol is joined to tower reactor, stock liquid adds in tower and distills, control tower bottom of rectifying tower temperature at 120 ~ 130 DEG C, absolute pressure is 0.05MPa, and reflux ratio is 3, end to be distilled, then add the stock liquid of same amount to distill.Collect respectively cut assay, oxime content is 99.88 ~ 99.96%, and in cut, foreign matter content is low.Within every 60 days, change a tower reactor solvent, column efficiency is stable, and in operational process, tower reactor is not coking.
Embodiment 15
Join mixing solutions same as Example 7 by the proportioning raw materials in example 7 and reagent dosage, add in rectifying tower and distill continuously with certain inlet amount, control tower bottom of rectifying tower temperature at 100 ~ 110 DEG C, absolute pressure is 0.01MPa, reflux ratio is 4, discharges after still liquid is processed and returns in tower and recycle simultaneously, timing acquiring cut assay with certain flow, oxime content is 99.77% ~ 99.91%, and foreign matter content is few.Column efficiency is stable, moves continuously 1 year tower reactor not coking.
Embodiment 16
Be ready to respectively reagent by the proportioning raw materials in example 8 and consumption, glycerine and heavy aromatic solvent oil are joined to tower reactor, stock liquid adds in tower and distills, control tower bottom of rectifying tower temperature at 150 ~ 160 DEG C, absolute pressure is 0.04MPa, reflux ratio is 2.5, end to be distilled, then add the stock liquid of same amount to distill.Collect respectively cut assay, oxime content is 99.87 ~ 99.98%, and in cut, foreign matter content is low.Within every 60 days, change a tower reactor solvent, column efficiency is stable, and in operational process, tower reactor is not coking.
Should be understood that these embodiment are only not used in and limit the scope of the invention for the present invention is described.In addition should be understood that those skilled in the art can make various changes or modifications the present invention after having read the content of the present invention's instruction, these equivalent form of values fall within the application's appended claims limited range equally.
Claims (5)
1. a distillating method for oxime, is characterized in that comprising the steps:
The first step: in the fractionation by distillation workshop section of oxime, in still-process, add in proportion a certain amount of high boiling solvent, maintaining high boiling solvent content in tower reactor is 0.02%～99%, and this high boiling solvent enters column distillation after can mixing with oxime, also can be directly adds separately arbitrary section of tower;
Second step: distill, collect cut, gained cut is refining oxime, and this operation can be that the oxime solution that contains high boiling solvent is added to rectifying tower, can be also the rectifying tower that adds tower reactor to contain high boiling solvent oxime;
The general formula of described oxime is R1 (C=NOH) R2, wherein R1 and R2 represent that carbonatoms is 1～10 alkyl, and described high boiling solvent is the organic solvent that is greater than the mixture of one or several solvents in 15～120 DEG C of petroleum hydrocarbons of oxime boiling point, high boiling point alcohols, ethers, ester class.
2. the distillating method of a kind of oxime according to claim 1, characterized by further comprising the 3rd step: not steaming the liquid of staying tower reactor in second step, recycle regularly removal of impurities as high boiling solvent.
3. the distillating method of a kind of oxime according to claim 1, is characterized in that distillation in second step is to carry out at absolute pressure 0～0.4MPa and 20～300 DEG C.
4. the distillating method of a kind of oxime according to claim 2, is characterized in that distillation in second step is to carry out at absolute pressure 0～0.4MPa and 20～300 DEG C.
5. the distillating method of a kind of oxime according to claim 1, is characterized in that described oxime is acetoxime, Diacetylmonoxime, methyl isobutyl ketoxime, methyl isoamyl ketoxime, 2 pentanone oxime, methyl-prop ketoxime.
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| MX2017013368A (en) * | 2015-04-20 | 2017-12-07 | Advansix Resins & Chemicals Llc | Coating composition including alkyl oximes. |
| CN106757137B (en) * | 2016-12-14 | 2018-10-26 | 重庆紫光化工股份有限公司 | A kind of clean preparation method and system of methylmercaptan ethyl aldoxime |
| CN107677765B (en) * | 2017-10-31 | 2020-07-14 | 浙江圣安化工股份有限公司 | Method for determining organic residue of hydroxylamine salt based on TOC (total organic carbon) derivatization catalytic combustion method |
| CN109627422B (en) * | 2018-11-19 | 2021-04-20 | 万华化学集团股份有限公司 | Preparation method of butanone oxime closed polyisocyanate |
| CN110423206B (en) * | 2019-07-17 | 2022-07-08 | 天津大学 | Method for separating cyclohexanone oxime, cyclohexanone and toluene from ammoximation reaction product |
| CN113292449B (en) * | 2021-05-29 | 2022-05-27 | 浙江锦华新材料股份有限公司 | Refining and purifying method of butanone oxime |
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Address after: 324012 No. 6, Nian Cheng Road, Quzhou hi tech Industrial Park, Zhejiang, China Patentee after: Zhejiang Sheng'an chemical Limited by Share Ltd Address before: 324000 Zhejiang province Kecheng District of Quzhou City High-tech Park reads the road No. 6 Patentee before: Zhejiang Sainon Chemical Co., Ltd. |